(R)-N-Cbz-2-allylprolyl(O-tert-butyl)tyrosine methyl ester

Base Information

• Chemical Name: (R)-N-Cbz-2-allylprolyl(O-tert-butyl)tyrosine methyl ester
• CAS No.: 121772-99-4
• Molecular Formula: C₃₀H₃₈N₂O₆
• Molecular Weight: 522.642
• Mol file: 121772-99-4.mol

Synonyms:(R)-N-Cbz-2-allylprolyl(O-tert-butyl)tyrosine methyl ester

Chemical Property of (R)-N-Cbz-2-allylprolyl(O-tert-butyl)tyrosine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-N-Cbz-2-allylprolyl(O-tert-butyl)tyrosine methyl ester

There total 4 articles about (R)-N-Cbz-2-allylprolyl(O-tert-butyl)tyrosine methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

O-tert-butyl-L-tyrosine methyl ester (52616-82-7) + (R)-N-(benzyloxycarbonyl)-2-(2'-propenyl)proline (121773-05-5) → (R)-N-Cbz-2-allylprolyl(O-tert-butyl)tyrosine methyl ester (121772-99-4)

Guidance literature:

With benzotriazol-1-ol; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; for 48h; Ambient temperature;

DOI:10.1021/jm00110a005

Reference yield:

(2R,5R)-5-allyl-2-tert-butyl-1-aza-3-oxabicyclo<3.3.0>octan-4-one (81286-83-1) → (R)-N-Cbz-2-allylprolyl(O-tert-butyl)tyrosine methyl ester (121772-99-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / 6 M aq. HCl / 48 h / Ambient temperature

2: 64 percent / Et₃N / acetonitrile; H₂O / 48 h / 0 °C

3: 95 percent / diisopropylcarbodiimide, hydroxybenzotriazole / dimethylformamide / 48 h / Ambient temperature

With hydrogenchloride; benzotriazol-1-ol; triethylamine; diisopropyl-carbodiimide; In water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm00110a005

Reference yield:

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (R)-N-Cbz-2-allylprolyl(O-tert-butyl)tyrosine methyl ester (121772-99-4)

Guidance literature:

Multi-step reaction with 3 steps

2: 50 percent / Et₃N

3: 95 percent / (i-Pr-N=)2C, HOBt / dimethylformamide

With benzotriazol-1-ol; triethylamine; diisopropyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1039/c39880001447

upstream raw materials:

O-tert-butyl-L-tyrosine methyl ester

(R)-N-(benzyloxycarbonyl)-2-(2'-propenyl)proline

(R)-2-allylpyrrolidine-2-carboxylic acid

L-proline

Downstream raw materials:

(S)-3-(4-tert-Butoxy-phenyl)-2-((R)-6-oxo-1,7-diaza-spiro[4.4]non-7-yl)-propionic acid methyl ester

(S)-2-{(R)-1-[(S)-2-tert-Butoxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionyl]-6-oxo-1,7-diaza-spiro[4.4]non-7-yl}-3-(4-tert-butoxy-phenyl)-propionic acid

(S)-2-{(R)-1-[(S)-2-tert-Butoxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionyl]-6-oxo-1,7-diaza-spiro[4.4]non-7-yl}-3-(4-tert-butoxy-phenyl)-propionic acid methyl ester

(S)-2-{(R)-1-[(S)-2-tert-Butoxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionyl]-6-oxo-1,7-diaza-spiro[4.4]non-7-yl}-3-(4-tert-butoxy-phenyl)-propionic acid pentafluorophenyl ester

Refernces

• 1、 Hinds,Welsh,Brennand,Fisher,Glennie,Richards,Turner,Robinson. "Synthesis, conformational, properties, and antibody recognition of peptides containing β-turn mimetics based on α-alkylproline derivates". . p. 1777 - 1789. Retrieved 2007/10/02.